The ultimate Tuscan adventure
Tuscany Highlights Tour
Follow the rhythm of the seasons from Chianti's rolling hills and elegant Lucca to the cypress valleys of the Val d’Orcia. This is the Tuscany you have always dreamed of.
Tour Details
Feel part of Tuscany as you discover the land, meet the people and take part in the celebrated traditions that have shaped this region for centuries.
Price
From US$9,950 per personGroup Size
Maximum 12 guestsDuration
10 days / 9 nightsDepartures
May/September 2027Starts/Ends
Florence to Rome
Inclusions
Boutique stays, guided experiences, and meals with wineAccommodation
Luxury agriturismo in the countryside and boutique hotel in LuccaActivity Level
Light walking — some uneven terrain
Highlights
Why You'll Love This Tour
Visit iconic Tuscan towns including Lucca, San Gimignano, Siena, Pienza, Montepulciano and discover smaller off-the-beaten-path ones along the way.
Meet the Tuscan locals who make Tuscany feel the way it does from a family-run iris and olive oil farm and a goat farm to the owner of a stunning private palazzo
Learn to make real Tuscan dishes in a family kitchen, learning timeless recipes passed down through generations.
Ride through cypress-lined roads in a vintage Fiat 500, the wind in your hair and Tuscany all around you.
Unwind completely - whether soaking in natural thermal baths or coasting through the countryside on an e-bike.
What our guests say
your untold italy tour Includes
9 nights in charming luxury 4 star accommodation – 2 nights in a boutique hotel in Lucca, 3 nights at a luxury agriturismo (countryhouse) in the Chianti countryside and 4 nights in a luxury agriturismo (countryhouse) in Val d’Orcia (Southern Tuscany)
Winery visits, Tuscan cooking class, cheese farm visit, visits to several Tuscan towns and villages, artisan workshop visits, Fiat 500 vintage car tour, thermal spa / e-bike tour, pizza making class and castle visit
9 breakfasts, 8 lunches, 1 aperitivo and 9 dinners as specified in the itinerary, wine and bottled water is included with meals other than breakfast.
Air-conditioned minibus/minivan will get you around on tour.
Tips and gratuities are included for local guides and your driver. Tips are not included for your tour host.
We pick up in central Florence and drop off in central Rome.
Not included
Fly into Rome or Milan. Florence can be reached in about 1.5 hours by fast-speed train.
No one books a trip expecting the unexpected – travel insurance ensures you’re covered if plans change. See our trip FAQ below for more information and suggested providers.
Nearly all meals are included – you’ll have two free lunches to explore the local food scene at your own pace.
Tour Overview
Tuscany Highlights Tour Description
Get to know the heart and soul of dreamy Tuscany, where days unfold between vine-covered hills, medieval towns, and cypress-lined valleys more beautiful than you could have ever imagined. From the rolling hills of classic Chianti to the golden fields of Val d’Orcia, this journey brings you behind the scenes and into the farms, artisan workshops, villas and around the tables of real Tuscans.
Vineyards, Villages, and Local Flavors
Wander through cobblestone villages and elegant towns like Lucca, San Gimignano, and Siena, where daily life is shaped by centuries-old traditions. Get to know the winemakers, cooks, and artisans who welcome you in and share their stories, their recipes, and their way of life. These are not just experiences to watch, but moments to take part in, whether you’re rolling pasta by hand or sitting down to a long lunch that stretches into the afternoon.
Hidden Corners and Slow Moments
Discover the beauty of the Val d’Orcia as you soak in thermal waters or e-bike through the valley and step inside the homes of hospitable locals eager to show you what it means to be Tuscan. Take part in a slower pace of life in the countryside, guided by the rhythm of the seasons.
Tuscany Highlights Tour Itinerary
We often don’t publish specific destinations in order to preserve the local flavor of your trip and allow you to enjoy special surprises along the way.
Day 1-2
Elegant Lucca and regal villas
Begin your Tuscan adventure in wonderful Lucca, a city of music and bikes, where medieval walls hold centuries of stories. Visit the villa once owned by Napoleon’s sister Elisa and enjoy a local opera performance, a moving tribute to the region’s rich culture.
See Details
- Places: San Miniato, Lucca
- Activities: Villa visit, Guided tour of Lucca and Puccini opera music performance
- Accommodation: Hotel Illaria (or similar)
Day 3-4
Chianti's Rolling Hills and Medieval Manhattan
Journey into the picturesque Chianti countryside, where iris flowers bloom in the spring and silvery olive trees shimmer in the autumn light. Visit a local iris/olive farm and discover the importance of both to the region – don’t leave without trying the ‘liquid gold’.
In the evening, raise a glass of Chianti at a family-owned winery, where dinner feels more like joining friends around the table. The next day, step into the workshop of a local artisan before exploring the medieval skyline of San Gimignano, its towers glowing in the late afternoon light.
See Details
- Places: Chianti countryside, Certaldo and San Gimignano
- Activities: Olive oil and iris farm visit, Winery visit and tasting, Artisan visit
- Accommodation: Querceto di Castellina (or similar)
Day 5-6
Tuscan Cheese and Wonderful Siena
At a family-run cheese farm, milk the goats and taste their creamy goat cheese straight from the source. Wander through a lively market village, chat with the locals, and end the day in a rustic kitchen where you’ll make wood-fired pizza – a delicious introduction to the flavors and warmth of rural Tuscany.
In nearby Siena, wander through medieval streets and learn about the city’s beloved Palio horse race, guided by locals who keep its traditions alive.
See Details
- Places: Greve in Chianti, Siena and Val d'Orcia countryside
- Activities: Guided walking tour, cheese farm visit and cheese making, pizza making
- Accommodation: Il Miraggio (or similar)
Day 7-8
Thermal baths, Fiat500 and Tuscan cooking
Walk through the doors of a historic palazzo and family-home in a charming small Tuscan town. Later, soak in natural thermal waters that have soothed travelers for centuries, or opt for a guided e-bike ride through the golden countryside
Whizz through the glorious countryside on a Fiat500 and have some time to wander pretty cheese-obsessed Pienza. Join a Tuscan cooking class in a welcoming country kitchen, where local ingredients tell their own stories. As you cook and taste alongside your host, you’ll feel part of a tradition that has flavored Tuscan tables for generations.
See Details
- Places: San Quirico, Bagno Vignoni, Pienza and Val d'Orcia countryside
- Activities: Palazzo visit, Fiat500 ride, thermal baths/e-bike ride, free time in Pienza, cooking class
- Accommodation: Il Miraggio (or similar)
Day 9-10
A Sweet Tuscan Farewell
Stroll through historic Montepulciano, taste the last true Vin Santo or ‘holy wine’ at a female-run winery and sink your teeth into the classic Tuscan ‘bistecca’.
Toast to your Tuscan adventures at a wonderful castle as you meet the women who still live there and hear the tales of their mighty ancestors.
See Details
- Places: Montepulciano, Tuscany countryside and Rome
- Activities: Montepulciano visit, Winery visit and tasting and castle visit
Over 1000+ satisfied guests
Departures
Upcoming Dates and Prices
Book now →Tuscany Highlight Tour
Mon 17 May - Wed 26 May 2027- Book now →
Tuscany Highlight Tour
Fri 24 Sep - Sun 3 Oct 2027
Private Tour
Private Tour
Get in touch for alternate dates
Request Itinerary
Want more information about this trip?
Enter your details and we’ll send you a complete PDF version of the Tuscany Highlights tour itinerary so you can start planning your escape to this beautiful region in central Italy.
Frequently Asked Questions
Your Tuscany Highlights tour departs in the morning from the Florence Santa Maria Novella train station at 10am.
Your Tuscany Highlights tour ends at Rome Termini station in the late afternoon.
Florence can be reached by high speed train in an hour and 30 minutes from Rome, and under two hours from Milan. If you prefer to travel by plane, the city has a small international airport that services Italian and European destinations.
Please let us know well in advance if you have any dietary needs, including allergies. It is quite a meat and dairy heavy cuisine so it can be a little difficult for vegetarians and not advisable for vegans. We’re happy to work with tour accommodation and restaurants to ensure that you have suitable meal options.
You’ll feel completely at home – whether you enjoy a glass of wine or prefer to skip it. Our tours celebrate the stories, traditions, and people behind Italy’s incredible food and wine culture, so there’s always something meaningful to experience. Non-alcoholic local options are happily provided, and every tasting, vineyard visit, or shared meal is about connection, not just what’s in the glass.
Absolutely! We always welcome solo travelers in our groups and generally have at least a couple of solo guests join.
This tour includes light to moderate physical activity, with guided walks lasting around 1–2 hours at a time. If you have mobility concerns, please get in touch and we can help you determine if this itinerary is the right fit.
Alongside USD, we offer payment in Australian, Canadian and New Zealand dollars, Euro and British pounds using the mid-market rate at time of payment on xe.com. Please reach out to us at info@untolditalytours for a quote.
Pay a USD $500 deposit per person to secure your place. Then three easy instalments at 180 days, 120 days and 90 days prior to departure or as specified on our tour booking page. The balance is due 60 days before departure or on the date specified on the trip booking page. Email us if you’d like to break up the instalments even more.
Your Tuscany Highlights tour offers unbeatable value for money and includes 4 star accommodation, luxury transportation, most meals, guided tours, entrance fees, artisan visits, local experiences, a dedicated tour host and more.
Most guests find they spend money on souvenirs, a few snacks and additional services such as laundry and spa treatments. You have one free time lunch but our guests often find this a welcome relief from the sheer amount of food during the rest of the tour.
When you book a tour with us, we take care of all the details so you can sit back, completely relax and enjoy your Italian experience..
Yes our 2027 tour schedule has several opportunities to combine this tour with another Untold Italy experience including our Cinque Terre and Beyond tours. In Spring, you can also combine this tour with Sicily or Northern Italy. Please reach out for more information.
The unexpected can occur and becoming ill or injured in a foreign country is a very daunting experience, therefore we require guests take insurance with international evacuation coverage for all trips.
Please consider cancelation insurance also because refunds are made available only per our
terms and conditions, and we are unable to make exceptions for any reason, including weather, injury/illness, or personal emergencies.
You should book a policy as soon as the trip has been confirmed. Some companies to consider:
- World Nomads – simple and flexible travel insurance for independent travelers. Includes 24×7 assistance when abroad
- Safety Wing Nomad Insurance – designed to meet the unexpected medical and travel needs faced by people traveling outside of their home country
- Travelex (USA residents only) – comprehensive travel insurance options covering medical assistance and delays
Unfortunately these providers may not offer policies for those aged over 69. In this case you can try Travel Insurance Master – a service that allows you to compare quotes and insurance policies.
Discover Tuscany
Tuscany needs no introduction, but, in the “untold” way, we like to go a little deeper. Discover Tuscany’s highlights and off the beaten path treasures when you read our articles and listen to our podcast about beautiful Tuscany.
Read
Tuscany Travel Guide
Uncover the highlights of the region
Listen
Spring Dishes from Tuscany
Learn about what we eat on this tour
